Win a date with Oliver Queen
by entersomethingcleverhere
Summary: Oliver's mother signs him up for a charity auction—much to his unending horror—and there's only one person who can save him from the terrible fate of getting auctioned off to one of his crazy stalkers. The only problem is convincing her to do it in the first place. [companion to P.S. I Hate You]


**A/N:** So this fic originally started off as an exercise meant to dispel some writer's block and it turned into...this.

This technically takes place during P.S. I Hate You, but it's not necessary to read before reading this (though I do suggest it).

Also, this is a belated birthday gift for the lovely Anna (Mimozka)! Happy birthday!

* * *

Oliver was screwed.

So _monumentally_ screwed.

And there was only one person in the city who could save him from this.

He didn't bother introducing himself before bursting through the door of her office. Eli had long since given up on trying to stop him, which meant she'd know it was him the minute she heard the door open.

And sure enough, the first words out of her mouth were, "Whatever it is, I'm not doing it."

She wasn't even looking up. She had her eyes still glued to the monitor in front of her, lines of neon green code scrolling upward like the freaking Matrix all while her fingers flew across her keyboard.

"Felicity." He was distinctly aware that his voice had taken on all the characteristics of a whine, but he didn't care. That's how dire this situation had become.

"I mean it, Oliver," she said, her eyes still on the computer, but her jaw slightly clenched as she reiterated her denial. "The last time I helped you out, I had to hack into three surveillance cameras and the SCPD database. In case you didn't know, those things are _illegal_."

"That is false," he protested. "You _wanted_ to hack the SCPD database just to see if you could."

She let out a huff of breath through her nose before she finally turned her stern glare toward him. "That's beside the point, Oliver. I can't afford to do you any more favors. My friendship with you is starting to ruin my reputation."

"See, you say _ruin_ , but what I hear is _elevating_."

Felicity rolled her eyes. "Get out."

Oliver sighed. So maybe it was true, and he had been asking for far too many heavy-handed favors of her recently. But the thing about being friends with her was that he knew just which buttons to push to get her to change her mind.

Crouching down in front of her desk, he looked up at her with his best pleading eyes. "Felicity," he whispered. "Please. Please, Felicity. I need you."

He could see the battle on her face, clear as day. She was trying _so hard_ to look everywhere else but in his eyes.

Deciding there was nothing for it now but to lay it on as thick as possible, he added, "You're the only one who can help me."

Those were the magic words that ended the battle on her face. She closed her eyes and with an angry, frustrated growl she answered, "Ugh! Fine! What do you want from me?"

Oliver immediately dropped all pretenses of a begging and jumped up happily to his feet. "OK, so here's what happened. You know the fundraiser thing the Starling City Chamber of Commerce is hosting next week?"

"Yeah," she trailed off warily. "Aren't they auctioning off dates with the CEOs of the biggest companies in the city or something like that?"

"It's not an auction," he grimaced. "It's a freaking meat market."

"Potato, po-tah-toe."

He rolled his eyes. "OK, well here's the thing: my mother in her infinite wisdom decided to sign me up for this thing against my wishes."

Felicity blinked in surprise for almost a full minute. Then when the words finally connected with her brain, she burst into wild, uncontrollable giggles.

"It's not funny!" Oliver protested.

"Au contraire," she managed to wheeze out despite her laughter. "The dreams of thousands of women all over the city will _finally_ come true! They have the chance to win the attentions of none other than Oliver Queen, the most eligible bachelor on the West Coast!"

He huffed out in annoyance. "All right, when you've finally decided to stop laughing at my pain, you'll see why I need your help."

She wiped away her tears of laughter. "Oliver, I don't see how I can really help you out with this one. Your mother already signed you up for this thing, and she's _really_ smart, so she's probably already put it out there in the media world that you're doing this thing so it would look really bad if you pulled out last minute or refused or something."

Trust Felicity to nail it in one.

"But there's still a way to save me," he insisted.

"I'm not helping you kill your mother."

"Would you let me finish?"

She fell silent at his outburst, one of her eyebrows raised and her red lips pursed with her skepticism.

"So here's my plan," he began. "I can't get out of it, you're right. But I _can_ rig the auction."

"How so?"

"By having _you_ bid on me."

Her eyes widened. "Oh...no…"

Oliver nodded. "Yes."

" _OLIVER!_ " she shrieked. "Are you freaking _kidding_ me?"

"What?" he demanded. "What's wrong with this plan?"

She sputtered in incredulity, like she was struggling to come up with the words. And knowing Felicity like he did, that was definitely a first.

"Think about it, it's brilliant!" he insisted. "I'll be able to save face by still going through with the dumb thing, but I won't have to sell myself on a glorified meat market to some rando I hardly know! It's perfect!"

That seemed to have jolted her out of her shock.

"You've lost your freaking mind!" she shouted. "First of all, there are going to be _hundreds_ of girls who will show up to this thing just for a chance to bid on you! _Hundreds_ , Oliver! You'll get auctioned off for thousands of dollars, probably _tens_ of thousands! And I while I realize that most of your friends don't even blink at dropping tens of thousands of dollars on a single date, need I remind you that I AM NOT ONE OF THEM!"

"I'll reimburse you for all of it," Oliver reasoned. "You won't have to worry about that."

"SECOND of all," she plowed on like he hadn't spoken, "this will completely ruin my reputation!"

"How so?" he demanded.

"Everyone in this company already thinks I'm sleeping with you! If I bid on you at this thing, the whole _city_ will think I'm sleeping with you!"

"No they won't," he scoffed. "No one would ever think for a million years that I would sleep with _you_."

The words were out of his mouth before he could even stop to consider their wisdom. His brain rushed to form an apology to undo the harm of his words, but it was already too late. Felicity's cheeks were red, and her eyes blazing with anger.

Without saying a word, she reached across her desk to grab the heavy black paperweight shaped like a pyramid on her desk and she chucked it hard at him.

Luckily he ducked at the last second.

"OK, I see now how that might be considered insulting," he began apologetically.

"YOU THINK?" she screeched.

This most definitely was not going according to plan.

If he had any hope of getting Felicity to agree to this thing, he was really going to have to think of a different tactic.

"I'm sorry, I'm sorry! I didn't mean to insult you, I just meant that everyone in the city knows that I'm really more into brunettes than blondes! Besides, everyone who's anyone knows that you're _way_ too smart to date a worthless pretty boy like me."

That seemed to temper her anger just the slightest bit. She pulled away from her desk slowly so she could regard him with cold, calculating eyes. Oliver used it as an opening to keep pleading his case.

"I will go to the greatest lengths to make it look like a platonic thing, Felicity," he promised, his hands clasped in front of him in a pleading position. "If anyone so much as asks, I'll swear up and down that you're nothing more than a friend. I'll hold a press conference for it, if that's what you need. Just...please. _Please_ save me from this."

She stared at him for what felt like forever. Oliver crossed all of his fingers behind his back, biting hard on his tongue and praying beyond all reasonable hope that she would say yes and save him from this complete and utter humiliation.

Finally, right as he was beginning to despair that she'd turned him down, Felicity spoke up.

"Fine, Oliver."

The relief flooded him like a breach in a dam.

"YES!" he shouted, throwing his fists in the air.

"But you owe me _so big_ ," she warned him. "I mean it, Queen."

"Yes, yes," Oliver nodded, not really paying attention to what she was saying. "I owe you big." Then, in his fit of gratitude, he leaned over her desk to peck her on the cheek.

"You, Felicity Smoak," he said in his most charming and wide smile, "are the best. The absolute _best_."

He could see her trying to fight the smile spreading across her face as she looked back at him. "Yeah," she answered. "I know."

* * *

The crowd at the annual Starling City Chamber of Commerce fundraiser could have been mistaken for the audience at a Beatles concert.

Only the fundraiser crowd was much better dressed.

Oliver sighed as he peeked through the curtain. The yahoos who organized the event rented out one of the big conference rooms at the Starling City Grand and set up a stage, complete with wings and everything. And in about twenty minutes, Oliver would be paraded onto that stage, like he was a specimen at a cattle auction or something.

Letting the curtain fall back, he pulled his phone out of his pocket and shot Felicity a quick text.

 _ARE YOU HERE YET?_

He paced back and forth until he got an answer about a minute later.

 _I'm pulling into the parking lot. Keep your pants on._

Then, a second later:

 _And stop pacing. You're going to wear a hole in the carpet_.

He couldn't help but smile at the text. She knew him too well.

"What the hell are you smiling about?" a voice said from behind him. Oliver turned around and found none other than Tommy Merlyn standing there with his eyebrows raised in confusion.

"Nothing," Oliver shook his head. "So I see you got roped into this as well."

"Roped in?" Tommy scoffed. "I volunteered!"

Oliver let out an incredulous laugh. "What? Why the hell would you _volunteer_ to do this?"

"Are you kidding? I get to sit back and watch a bunch of women fight over me. And what's better, it's for a good cause." Tommy shot him a smug smile as he adjusted his cuffs under his sports coat. "What could be better?"

Oliver rolled his eyes. Trust Tommy to take his objectification as a compliment.

"Though I will say, now that I know you're part of this thing, my status as the big ticket item at this auction is in serious jeopardy."

Oliver couldn't help but laugh at that.

"Who else is being auctioned off anyway?"

Tommy glanced around with a grimace. "From the looks of it, not very many guys who'd be worth the money," he whispered to his best friend.

Right at that moment, Oliver spotted Carter Bowen from the other side of the room, chatting up some bored soul who looked like he'd rather be anywhere than talking with that pompous jackass.

Tommy turned to look where Oliver was staring, then let out a groan. "Oh God," he muttered. "Who let Dr. Carter Blow-me in?"

"I think he's one of the guys getting auctioned off," Oliver responded with a grimace.

"Oh, well I _definitely_ have to get sold for more than him," Tommy muttered under his breath.

Oliver stared at his best friend. "I want you to stop and replay that sentence in your head. Then I want you to stop talking for the rest of the evening."

A buzz in his pocket drew Oliver's attention to a new text from Felicity. His stomach dropped to his ankles when he read it.

 _Heads up,_ it said. _Carrie Cutter's here_.

"Fuck!" Oliver bit out.

This was the absolute _worst_ case scenario.

"What?" Tommy asked, craning his neck over Oliver's shoulder. "What's going on?"

"Carrie's here," Oliver muttered, showing his friend the text.

Tommy's eyes widened for a millisecond as he read the message. Then, when the shock passed, he burst out into uncontrollable laughter.

"It's not funny!" Oliver protested.

Tommy couldn't respond for how hard he was laughing.

"Shut up, you asshole!" he hissed. "It's _not_ funny! This is Carrie Cutter we're talking about! Don't you remember how she _miraculously_ got into my apartment and waited there for me, naked on my bed with a roll of duct tape and a knife?"

That only made Tommy laugh harder.

Oliver gritted his teeth, turning his attention back to his phone.

 _You HAVE to outbid her!_ he texted back. _I don't care how much it takes!_

 _Don't worry,_ she responded. _I'm not letting you go home with this psychopath._

* * *

Oliver really hadn't been kidding when he called it a meat market.

Felicity looked around the vast hall in the Starling Grand. It was practically filled to the hilt with what felt like every eligible bachelorette in Starling City. Dressed in their fancy cocktail dresses, they all milled about politely chit chatting with one another, but she knew better. The conversations were less about making friends and more about sizing up the competition. Every woman here had an agenda, and the more ruthless ones would stop at nothing to get what they wanted.

In Oliver's analogy, the men being auctioned off were the meat. The women at the event were the vultures.

At the very least, it was one of the lovelier meat markets Felicity had ever attended. The chamber of commerce had turned the nondescript room into what could only be described as a cross between a fashion show and a cocktail reception. There was a huge stage right at the front that bisected the room with the long runway. Then there were small cocktail tables scattered all around the room, perhaps fifty in all with tiny arrangements of dusky pink-petaled lilies.

Hoping to avoid any conversation with one of the more aggressive vultures, Felicity grabbed a champagne flute off the tray of a traveling waiter and retreated to the far corner with her phone. She wasn't here to secure a date for real. She was only here to help a friend.

That was it.

She sipped on her champagne as she scrolled through her Twitter feed, trying to catch up on the Apple presentation that happened earlier that day. But she didn't get far into the announced specs when she felt the presence of another human being standing right in front of her.

Looking up from her phone, she saw a beautiful woman with deep red hair and wide blue eyes. She wore a bright green cocktail dress that flared out at her waist, paired with gold pumps with heels sharp enough to gouge a man's eyes out.

"Hi," she said brightly as she held out her hand. "I'm Carrie. Carrie Cutter."

Felicity felt her eyes widen slightly at the name.

Well, maybe Oliver was right to freak out about this thing.

Carrie tilted her head to the side and Felicity realized with a start that Carrie still had her hand outstretched. Transferring her champagne flute, she shook Carrie's proffered hand. "Hi, it's nice to meet you. I'm Felicity Smoak."

"Oh yes, I've heard of you," Carrie responded. Her voice was light and sweet, but her handshake had the slightest bit of pressure. "Aren't you the head of applied sciences at Queen Consolidated?"

"Um, yeah," Felicity answered uncomfortably. She desperately wanted her hand back, but Carrie didn't seem inclined to release it any time soon.

"I've seen your picture on a couple of the tabloids," she continued. Her beautiful blue eyes started flashing with just the tiniest bit of malice. "You're very good friends with Oliver Queen, aren't you?"

"We are," Felicity responded. She pulled a little to get Carrie to release her hand, but the woman only clamped down harder.

"So is it safe to say that you're planning on bidding on him tonight?"

"Not that it's any of your business, but yes." Felicity was growing increasingly uncomfortable with Carrie's proximity. With each question, she stepped closer and closer until she was just inches away, and Felicity could see the crazy flashing in the other woman's eyes.

"Well you're not going to win him," Carrie answered. Her smile had taken on the characteristic of a deranged clown. "He's _my_ lover."

"OK, but the last time I checked, he had you arrested because you broke into his apartment and tied yourself naked to his bed. So you'll excuse me if I believe he's up for grabs."

Felicity winced at her own words. Up for _grabs_? she thought incredulously to herself. Jesus Christ, she sounded like the protagonist of some shitty teen movie.

Besides, if Oliver were here he would be so smug at how she was fighting this crazy woman over him. She wanted to pound her head against something.

But Felicity's words had the desired effect, at least. Carrie finally let go of her hand, but she stepped even closer until their faces were practically touching. She'd also let go of all pretense of politeness, instead scowling at Felicity with complete and utter disdain.

"You better not try to outbid me tonight," she snarled. "I will end you, do you understand? Oliver Queen is _mine_ , and I won't let him go home with anyone else."

Despite her discomfort at Carrie's proximity, Felicity felt her hackles raise and her protective instincts kick in. Oliver might have been her annoying friend, but he was still her friend nonetheless. She wasn't about to hand him over to this...this _harpy_ without a fight.

And even if she lost the fight, she'd come back and claw her eyes out.

"Oliver Queen doesn't belong to anyone, least of all the psychopath who thought the best way to seduce him was to commit a felony," she shot back. "And I'm not afraid of you, Carrie. So why don't you go threaten someone else?"

Carrie clenched her teeth as she stepped away. "Watch your back, Felicity Smoak," she growled. And with that, she turned on her insane heel and stomped off.

Felicity let out a deep breath, then swiped her phone on. Time to warn Oliver just what he was in for tonight.

* * *

Of course they were going to do this thing by alphabetical order, Oliver thought angrily to himself. God forbid they put him out of his misery early. No, instead they'd make him wait through the auction of twelve other guys before he could get this godforsaken thing over with.

Oliver watched in the wings as each man stepped up to the butcher's block. The first few guys sold for a modest amount ("Ha! Dr. Blow-me only went for two hundred!" Tommy shouted triumphantly), but the minute Tommy stepped up to the plate, it was like all the women at the event emerged out of hibernation.

The bidding started off at fifty dollars like everyone else, but it quickly climbed, increasing by increments of one hundred dollars each time. By the time it hit two thousand, it was down to two women who looked like they were going to lunge across the stage at each other to claw the other woman's eyes out.

"FIVE THOUSAND!" the woman on the left finally screamed.

The entire room fell silent at her declaration.

"Five thousand!" the emcee shouted gleefully. "Five thousand, any takers? Five thousand going once! Five thousand going twice! _Sold_ to that lucky young woman in the blue, yes, congratulations!"

Oliver grimaced as the room clapped and Tommy stepped off the stage to meet the (un)lucky woman who won his companionship. Tommy was definitely the one who'd been sold for the most so far.

He hoped his own bidding war wouldn't drag on for nearly as long.

Two more men stepped up for auction, and then finally, it was Oliver's turn. With dread weighing heavily in every cell in his body, he dragged his reluctant feet out of the wings and onto the stage.

"Next up is none other than Oliver Queen!" the emcee announced. The crowd of women suddenly became way more animated, screaming and clapping with excitement. It only made his dread increase tenfold.

"You all know him as the heir to the Queen Consolidated throne, but let's hear a little bit about the man from the man himself!" the emcee threw his arm around Oliver, who recoiled from the touch.

"Oliver, tell us about yourself," he said as he shoved the microphone up in his face. "How does your perfect date end?"

"No one dies," he deadpanned.

A laugh rippled through the audience. He was being sarcastic on purpose, but everyone found it charming.

This was his worst nightmare.

"Well then, let's go ahead and get the bidding started! We'll start with fif — "

"Fifty!" someone shouted immediately.

"One hundred!" someone else countered.

"One hundred fifty!" a different voice piped in.

The bidding started pretty much immediately, and the emcee didn't even have the chance to facilitate it. The minute one woman threw in her bid, someone else upped it. And it was among an alarmingly wide range of women — Oliver counted at least ten in the beginning. At one point he was pretty sure one of the consistent bidders was Thea's childhood best friend (much to his alarm), but she dropped out of the bidding once it hit five hundred dollars.

Felicity seemed to be biding her time, and Oliver couldn't blame her. But he also was starting to get really antsy, because Carrie hadn't submit a bid yet either.

The price eventually surpassed Tommy's. Soon it was at six thousand, and though bidders were dropping off one by one, there were still enough to send it up to seven thousand. Then eight.

"Ten thousand!" a new voice chimed in. Much to Oliver's horror, the bid came from none other than a smug Carrie Cutter.

"Wow, _ten thousand_!" the emcee shouted gleefully. "Any takers?"

"Ten five," a new voice announced.

Oliver had never been more relieved to hear Felicity's voice in his entire life.

Carrie shot an angry glare at the woman who outbid her. "Eleven thousand!"

"Eleven five," Felicity responded.

Carrie was practically growling at this point. "Fifteen thousand!" she screamed.

"Fifteen-five," Felicity answered.

Carrie's face scrunched up in anger, until she finally shouted, "TWENTY THOUSAND!"

Oliver's eyes were trained on Felicity. She had spent the entire bidding war staring at Carrie with cool disregard, but suddenly her face took on all the characteristics of a predatory stalking its prey. Her eyebrows had furrowed in concentration, and Felicity's blue eyes were alight with some kind of fiery determination.

He couldn't help but feel a little bit mesmerized by the sight.

"Fifty thousand," she announced.

That drew a gasp from everyone in the room, and Oliver couldn't help but feel intense relief and pleasure as the blood drained from Carrie's face.

"Fifty _thousand dollars_!" the emcee screeched. "Fifty thousand dollars going once! Twice!"

Oliver bit down on his cheek and crossed every finger in his pockets, praying to deities he didn't believe in that this would be the end of this godforsaken exercise in humiliation.

"SOLD to that lovely young woman in red! Congratulations to you, my dear!"

Oliver jumped off the stage eagerly, making his way through the crowd of people to Felicity. In that moment, she was like his beacon. His shining pillar of hope that saved him from the worst of fates.

The minute he reached her, he wrapped her in a bear hug and squeezed her tightly to him.

"Thank you," he whispered fervently. "You saved me."

He felt rather than heard her chuckle as her arms went up to wrap around him in return. "You're welcome, Oliver."


End file.
